CA2387724A1 - Method for preparing a benzofuran or benzothiophene compound - Google Patents
Method for preparing a benzofuran or benzothiophene compound Download PDFInfo
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- CA2387724A1 CA2387724A1 CA002387724A CA2387724A CA2387724A1 CA 2387724 A1 CA2387724 A1 CA 2387724A1 CA 002387724 A CA002387724 A CA 002387724A CA 2387724 A CA2387724 A CA 2387724A CA 2387724 A1 CA2387724 A1 CA 2387724A1
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- aromatic
- anhydride
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- 238000000034 method Methods 0.000 title claims abstract 27
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims abstract 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N thianaphthalene Natural products C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims abstract 5
- -1 benzothiophene compound Chemical class 0.000 title claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 25
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 238000007363 ring formation reaction Methods 0.000 claims abstract 5
- 150000008064 anhydrides Chemical class 0.000 claims abstract 4
- 239000003960 organic solvent Substances 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 3
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 3
- 239000001301 oxygen Substances 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 150000002430 hydrocarbons Chemical group 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 239000000758 substrate Substances 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims 1
- XGAJABPTUOLUAE-UHFFFAOYSA-N 2-butyl-5-nitro-1-benzofuran Chemical compound [O-][N+](=O)C1=CC=C2OC(CCCC)=CC2=C1 XGAJABPTUOLUAE-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 150000008378 aryl ethers Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 150000002828 nitro derivatives Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/10—Cyclisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
La présente invention a pour objet un nouveau procédé de préparation d'un composé de type benzofurane ou benzothiophène par cyclisation d'un composé aromatique porteur d'une part, d'une chaîne latérale comprenant au moins deu x atomes de carbone, l'un des atomes de carbone étant relié au cycle benzéniqu e par un atome d'oxygène ou de soufre, l'autre atome de carbone est sous forme carboxylique et d'autre part d'un groupe formyle en position ortho par rappo rt à ladite chaîne. Le procédé de l'invention est caractérisé par le fait qu'il consiste à effectuer la cyclisation de ce dernier, en présence d'une quantit é efficace d'une base de type carbonate, dans un milieu comprenant un anhydrid e d'acide carboxylique et éventuellement un solvant organique.The subject of the present invention is a new process for the preparation of a compound of the benzofuran or benzothiophene type by cyclization of an aromatic compound carrying on the one hand, a side chain comprising at least two x carbon atoms, one carbon atoms being linked to the benzene ring by an oxygen or sulfur atom, the other carbon atom is in carboxylic form and on the other hand a formyl group in the ortho position with respect to said chain. The process of the invention is characterized in that it consists in carrying out the cyclization of the latter, in the presence of an effective quantity of a base of carbonate type, in a medium comprising an anhydride of carboxylic acid. and optionally an organic solvent.
Claims (24)
caractérisé par le fait qu'il consiste à effectuer la cyclisation de ce dernier, dans un milieu comprenant un anhydride d'acide carboxylique et en présence d'une base choisie parmi les carbonates et/ou hydrogénocarbonates métalliques ou d'ammonium. 1 - Process for the preparation of a compound of the benzofuran type or benzothiophene from an aromatic compound carrying on the one hand, a side chain comprising at least two carbon atoms, one of carbon atoms being linked to the benzene ring by an oxygen atom or sulfur, the other carbon atom is in carboxylic form and other part of a formyl group in position ortho with respect to said chain.
characterized by the fact that it consists in carrying out the cyclization of this latest, in a medium comprising a carboxylic acid anhydride and in the presence a base chosen from carbonates and / or hydrogen carbonates metallic or ammonium.
aromatique de départ répond à la formule suivante:
dans ladite formule (I):
- R1 représente un atome d'hydrogène, un groupe alkyle linéaire ou ramifié
ayant de 1 à 12 atomes de carbone, un groupe phényle éventuellement substitué par un groupe alkyle ayant de 1 à 4 atomes de carbone ou un groupe halogénophényle, - Z représente un atome d'oxygène ou de soufre, - R représente un atome d'hydrogène ou un substituant, - n est un nombre égal à 0,1, 2, ou 3, de préférence, égal à 0, - lorsque n est supérieur à 1, deux groupes R et les 2 atomes successifs du cycle benzénique peuvent former entre eux un cycle saturé, insaturé ou aromatique ayant de 5 à 7 atomes de carbone. 2 - Method according to claim 1 characterized in that the compound starting aromatic meets the following formula:
in said formula (I):
- R1 represents a hydrogen atom, a linear or branched alkyl group having from 1 to 12 carbon atoms, a phenyl group optionally substituted by an alkyl group having 1 to 4 carbon atoms or a halophenyl group, - Z represents an oxygen or sulfur atom, - R represents a hydrogen atom or a substituent, - n is a number equal to 0.1, 2, or 3, preferably equal to 0, - when n is greater than 1, two R groups and the 2 successive atoms of benzene cycle can form a saturated, unsaturated or aromatic having 5 to 7 carbon atoms.
- un groupe nitro, - un groupe hydroxyle, - un groupe alkyle linéaire ou ramifié, ayant de 1 à 6 atomes de carbone, de préférence de 1 à 4 atomes de carbone, tel que méthyle, éthyle, propyle, isopropyle, butyle, isobutyle, sec-butyle, tert-butyle, - un groupe alkoxy ayant de 1 à 6 atomes de carbone, de préférence de 1 à 4 atomes de carbone, - un groupe ester ayant de 1 à 10 atomes de carbone, de préférence de 1 à 4 atomes de carbone, - un groupe alkylamide ayant de 1 à 6 atomes de carbone, de préférence 1 à 4 atomes de carbone, - un groupe carboxamide, - un atome d'halogène, - un groupe trifluorométhyle. 3 - Method according to claim 2 characterized in that R represents a hydrogen atom or one of the following groups:
- a nitro group, - a hydroxyl group, - a linear or branched alkyl group having from 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, - an alkoxy group having from 1 to 6 carbon atoms, preferably from 1 with 4 carbon atoms, - an ester group having from 1 to 10 carbon atoms, preferably from 1 with 4 carbon atoms, - an alkylamide group having from 1 to 6 carbon atoms, preferably 1 with 4 carbon atoms, - a carboxamide group, - a halogen atom, - a trifluoromethyl group.
dans laquelle:
- R1 représente un groupe alkyle linéaire ou ramifié ayant de 1 à 12 atomes de carbone, un groupe phényle éventuellement substitué par un groupe alkyle ayant de 1 à 4 atomes de carbone ou un groupe halogénophényle, - R2 représente un atome d'hydrogène, un groupe hydrocarboné ayant de 1 à 12 atomes de carbone qui peut être un groupe alkyle linéaire ou ramifié, un groupe cycloalkyle, un groupe phényle ou un groupe phénylalkyle, - Z représente un atome d'oxygène ou de soufre, - R représente un atome d'hydrogène ou un substituant, - n est un nombre égal à 0,1, 2, ou 3, de préférence, égal à 0, - lorsque n est supérieur à 1, deux groupes R et les 2 atomes successifs du cycle benzénique peuvent former entre eux un cycle saturé, insaturé ou aromatique ayant de 5 à 7 atomes de carbone. 4 - Method according to one of claims 2 and 3 characterized in that the starting aromatic compound corresponds to the following formula:
in which:
- R1 represents a linear or branched alkyl group having from 1 to 12 atoms carbon, a phenyl group optionally substituted by a group alkyl having from 1 to 4 carbon atoms or a halophenyl group, - R2 represents a hydrogen atom, a hydrocarbon group having 1 with 12 carbon atoms which can be a linear or branched alkyl group, a cycloalkyl group, a phenyl group or a phenylalkyl group, - Z represents an oxygen or sulfur atom, - R represents a hydrogen atom or a substituent, - n is a number equal to 0.1, 2, or 3, preferably equal to 0, - when n is greater than 1, two R groups and the 2 successive atoms of benzene cycle can form a saturated, unsaturated or aromatic having 5 to 7 carbon atoms.
représente un atome d'hydrogène, un groupe méthyle ou éthyle, un groupe méthoxy ou éthoxy. 5- Method according to one of claims 2 and 4 characterized in that R
represents a hydrogen atom, a methyl or ethyl group, a group methoxy or ethoxy.
dans ladite formule (VI):
- R a et R b, identiques ou différents, représentent un groupe hydrocarboné
monovalent, substitué ou non qui peut être un groupe aliphatique acyclique, saturé ou insaturé, linéaire ou ramifié ; un groupe carbocyclique saturé, insaturé ou aromatique, monocyclique, - R a et R b pouvant former ensemble un groupe divalent aliphatique saturé
ou insaturé, linéaire ou ramifié, ayant au moins 2 atomes de carbone. 8- A method according to claim 1 characterized in that the anhydride of carboxylic acid corresponds to the following formula:
in said formula (VI):
- R a and R b, identical or different, represent a hydrocarbon group monovalent, substituted or not which can be an aliphatic group acyclic, saturated or unsaturated, linear or branched; a carbocyclic group saturated, unsaturated or aromatic, monocyclic, - R a and R b can together form a divalent saturated aliphatic group or unsaturated, linear or branched, having at least 2 carbon atoms.
- Procédé selon la revendication 8 caractérisé par le fait que l'anhydride carboxylique est un anhydride non cyclique répondant à la formule (VI), dans laquelle les groupes R a et R b, identiques ou différents représentent - un groupe aliphatique acyclique linéaire ou ramifié ayant de préférence de 1 à 24, de préférence, de 1 à 12 atomes de carbone, saturé ou comprenant une à plusieurs insaturations sur la chaîne, généralement, 1 à
3 insaturations qui peuvent être des doubles liaisons simples: la chaîne hydrocarbonée pouvant être interrompue par l'un des groupes suivants -O-; -CO-; et/ou porteuse d'un ou plusieurs substituants notamment : -X;
-CX3. 9 - Process according to claim 8 characterized in that the anhydride carboxylic is a cyclic anhydride having 5 to 10 atoms in the ring does not comprising or comprising a double bond, one of the atoms possibly be replaced by an oxygen atom.
- Method according to claim 8 characterized in that the anhydride carboxylic is a non-cyclic anhydride corresponding to formula (VI), in which the groups R a and R b, which are identical or different, represent a linear or branched acyclic aliphatic group preferably having 1 to 24, preferably from 1 to 12 carbon atoms, saturated or comprising one to several unsaturations on the chain, generally 1 to 3 unsaturations which can be simple double bonds: the chain hydrocarbon which can be interrupted by one of the following groups -O-; -CO-; and / or carrying one or more substituents, in particular: -X;
-CX3.
effectuer la cyclisation du substrat de départ en l'absence ou en présence d'un solvant organique. 14 - Method according to claim 1 characterized in that it consists of cyclize the starting substrate in the absence or presence of a organic solvent.
l'hexaméthylphosphotriamide (HMPT); la tétraméthylurée; les composés nitrés;
les nitriles aliphatiques ou aromatiques; la tétraméthylène sulfone (sulfolane);
et les mélanges des différents solvants précités. 15 - Process according to claim 14 characterized in that the solvent organic is chosen from: aromatic hydrocarbons, halogenated or not, aliphatic, cycloaliphatic or aromatic ether oxides linear or cyclic carboxamides dimethyl sulfoxide (DMSO);
hexamethylphosphotriamide (HMPT); tetramethylurea; nitro compounds;
aliphatic or aromatic nitriles; tetramethylene sulfone (sulfolane);
and mixtures of the various solvents mentioned above.
d'anhydride d'acide carboxylique mise en oeuvre est telle que le rapport molaire anhydride d'acide carboxylique/composé de formule (I) varie entre 1 et 3. 17 - Process according to claim 14 characterized in that the quantity of carboxylic acid anhydride used is such that the ratio molar carboxylic acid anhydride / compound of formula (I) varies between 1 and 3.
de solvant organique à mettre en oeuvre est déterminée de telle sorte que la concentration du substrat dans le solvant organique soit de préférence comprise entre 1 et 5 mol/litre et plus préférentiellement entre 2 et 3 mol/litre. 18 - Process according to claim 14 characterized in that the quantity of organic solvent to be used is determined so that the concentration of the substrate in the organic solvent is preferably between 1 and 5 mol / liter and more preferably between 2 and 3 mol / liter.
dans ladite formule (V), R, R1, Z et n ont la signification donnée précédemment dans l'une des revendications 2 à 5. 22 - Method according to one of claims 1 to 20 characterized in that the cyclized product corresponds to the following formula (V):
in said formula (V), R, R1, Z and n have the meaning given previously in one of claims 2 to 5.
dans ladite formule (V'), R, R1, Z et n ont la signification donnée précédemment dans l'une des revendications 2 à 5. 23 - Method according to one of claims 1 to 20 characterized in that the cyclized product corresponds to the following formula (V '):
in said formula (V '), R, R1, Z and n have the meaning given previously in one of claims 2 to 5.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9913251A FR2800064B1 (en) | 1999-10-21 | 1999-10-21 | PROCESS FOR THE PREPARATION OF A BENZOFURANE OR BENZOTHIOPHENE COMPOUND |
| FR99/13251 | 1999-10-21 | ||
| FR0006629A FR2809397B1 (en) | 2000-05-24 | 2000-05-24 | PROCESS FOR THE PREPARATION OF A BENZOFURAN OR BENZOTHIOPHENE COMPOUND |
| FR00/06629 | 2000-05-24 | ||
| PCT/FR2000/002947 WO2001029019A1 (en) | 1999-10-21 | 2000-10-23 | Method for preparing a benzofuran or benzothiophene compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2387724A1 true CA2387724A1 (en) | 2001-04-26 |
| CA2387724C CA2387724C (en) | 2011-09-20 |
Family
ID=26212419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2387724A Expired - Fee Related CA2387724C (en) | 1999-10-21 | 2000-10-23 | Method for preparing a benzofuran or benzothiophene compound |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6555697B1 (en) |
| EP (1) | EP1222181B1 (en) |
| JP (1) | JP2003512365A (en) |
| CN (1) | CN1200935C (en) |
| AT (1) | ATE256118T1 (en) |
| AU (1) | AU1033101A (en) |
| BR (1) | BR0014810A (en) |
| CA (1) | CA2387724C (en) |
| DE (1) | DE60007164T2 (en) |
| ES (1) | ES2213050T3 (en) |
| HU (1) | HUP0203205A3 (en) |
| PT (1) | PT1222181E (en) |
| WO (1) | WO2001029019A1 (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002230409A1 (en) * | 2000-11-27 | 2002-06-03 | Eli Lilly And Company | Process for preparing 3-aryl-benzo(b)thiophenes |
| IL146389A0 (en) | 2001-11-08 | 2002-07-25 | Isp Finetech Ltd | Process for the preparation of dronedarone |
| DE10237819A1 (en) * | 2002-08-19 | 2004-03-04 | Bayer Ag | 5-Nitrobenzofurane |
| US6960669B2 (en) * | 2003-09-10 | 2005-11-01 | Crompton Co./Cie | Utilization of phosphorus pentasulfide in thionylations using phase transfer catalysis |
| FR2914643B1 (en) * | 2007-04-06 | 2009-06-05 | Finorga Soc Par Actions Simpli | PROCESS FOR THE PREPARATION OF 2- (N-BUTYL) -5-NITROBENZOFURAN |
| FR2915482B1 (en) * | 2007-04-27 | 2009-11-27 | Finorga | PROCESS FOR THE PREPARATION OF 2- (N-BUTYL) -5-NITROBENZOFURANE |
| TW201111354A (en) | 2009-05-27 | 2011-04-01 | Sanofi Aventis | Process for the production of Dronedarone intermediates |
| UY32656A (en) | 2009-05-27 | 2010-12-31 | Sanofi Aventis | PROCEDURE TO PRODUCE BENZOFURANS |
| FR2958290B1 (en) | 2010-03-30 | 2012-10-19 | Sanofi Aventis | PROCESS FOR THE PREPARATION OF SULFONAMIDO-BENZOFURAN DERIVATIVES |
| HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
| WO2012032545A1 (en) | 2010-09-08 | 2012-03-15 | Cadila Healthcare Limited | Processes for preparing dronedarone and its intermediates |
| WO2012120544A2 (en) | 2011-03-10 | 2012-09-13 | Sun Pharmaceutical Industries Ltd. | PROCESS FOR N-[2-n-BUTYL-3-[4-[3-(DI-n-BUTYLAMINO) PROPOXY]ENZOYL]BENZOFURAN-5-YL]METHANESULFONAMIDE HYDROCHLORIDE |
| HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
| HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
| FR2983198B1 (en) | 2011-11-29 | 2013-11-15 | Sanofi Sa | PROCESS FOR THE PREPARATION OF 5-AMINO-BENZOYL-BENZOFURAN DERIVATIVES |
| EP2617718A1 (en) | 2012-01-20 | 2013-07-24 | Sanofi | Process for preparation of dronedarone by the use of dibutylaminopropanol reagent |
| US9221778B2 (en) | 2012-02-13 | 2015-12-29 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
| US9249119B2 (en) | 2012-02-14 | 2016-02-02 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
| US9382223B2 (en) | 2012-02-22 | 2016-07-05 | Sanofi | Process for preparation of dronedarone by oxidation of a hydroxyl group |
| US9238636B2 (en) | 2012-05-31 | 2016-01-19 | Sanofi | Process for preparation of dronedarone by Grignard reaction |
| CN108675972B (en) * | 2018-08-01 | 2020-09-11 | 北京嘉林药业股份有限公司 | Preparation method of amiodarone hydrochloride intermediate 2-butyl benzofuran |
| CN110483871A (en) * | 2019-08-15 | 2019-11-22 | 陈全明 | A kind of HDPE double-wall corrugated pipe of anti-pressure and abrasion-proof |
| CN114539193B (en) * | 2022-01-20 | 2024-08-06 | 安徽普利药业有限公司 | Preparation method of amiodarone hydrochloride intermediate |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577441A (en) | 1967-03-07 | 1971-05-04 | Warner Lambert Pharmaceutical | Nitro substituted benzofurans |
| DE3031738A1 (en) * | 1980-08-22 | 1982-04-01 | Troponwerke GmbH & Co KG, 5000 Köln | Benzothiophene derivs. prodn. - by cyclisation of 2-acyl-phenylthio-acetic acid cpds. using carboxylic acids e.g. propionic acid as condensation agent |
| FR2665444B1 (en) | 1990-08-06 | 1992-11-27 | Sanofi Sa | AMINO-BENZOFURAN, BENZOTHIOPHENE OR INDOLE DERIVATIVES, THEIR PREPARATION PROCESS AND THE COMPOSITIONS CONTAINING THEM. |
| FR2800067B1 (en) * | 1999-10-21 | 2004-12-17 | Rhodia Chimie Sa | INTERMEDIATES FOR THE MANUFACTURE OF A BENZOFURANE OR NITROGEN BENZOTHIOPHENE DERIVATIVE IN POSITION 5 AND THEIR USES |
-
2000
- 2000-10-23 JP JP2001531819A patent/JP2003512365A/en active Pending
- 2000-10-23 HU HU0203205A patent/HUP0203205A3/en unknown
- 2000-10-23 WO PCT/FR2000/002947 patent/WO2001029019A1/en active IP Right Grant
- 2000-10-23 EP EP00971484A patent/EP1222181B1/en not_active Expired - Lifetime
- 2000-10-23 BR BR0014810-5A patent/BR0014810A/en not_active Application Discontinuation
- 2000-10-23 ES ES00971484T patent/ES2213050T3/en not_active Expired - Lifetime
- 2000-10-23 CA CA2387724A patent/CA2387724C/en not_active Expired - Fee Related
- 2000-10-23 PT PT00971484T patent/PT1222181E/en unknown
- 2000-10-23 AT AT00971484T patent/ATE256118T1/en not_active IP Right Cessation
- 2000-10-23 AU AU10331/01A patent/AU1033101A/en not_active Abandoned
- 2000-10-23 US US10/110,443 patent/US6555697B1/en not_active Expired - Fee Related
- 2000-10-23 CN CNB008145709A patent/CN1200935C/en not_active Expired - Fee Related
- 2000-10-23 DE DE60007164T patent/DE60007164T2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1222181B1 (en) | 2003-12-10 |
| CN1382133A (en) | 2002-11-27 |
| ES2213050T3 (en) | 2004-08-16 |
| EP1222181A1 (en) | 2002-07-17 |
| DE60007164D1 (en) | 2004-01-22 |
| US6555697B1 (en) | 2003-04-29 |
| CA2387724C (en) | 2011-09-20 |
| AU1033101A (en) | 2001-04-30 |
| BR0014810A (en) | 2002-06-11 |
| HUP0203205A3 (en) | 2003-04-28 |
| CN1200935C (en) | 2005-05-11 |
| JP2003512365A (en) | 2003-04-02 |
| DE60007164T2 (en) | 2004-09-16 |
| ATE256118T1 (en) | 2003-12-15 |
| WO2001029019A1 (en) | 2001-04-26 |
| PT1222181E (en) | 2004-04-30 |
| HUP0203205A2 (en) | 2003-03-28 |
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